This is a prime example of one of my favoured spring/summer looks, because it’s one that says, “I wish I was on vacation,” which is basically what I’m thinking at all times.

The nautical stripes represent my need to be by the water (on a yacht) and the tropical print shows my longing to be on a sandy beach (near an all-inclusive bar). The jean jacket and heels? I guess those are the city-appropriate reminders that bring me back down to earth.

Mixing prints is a huge trend for the season, and it’s one of the most fun ways to challenge yourself. When it comes to trying to make prints work, I like to remind myself of a quote from one of Henry Holland’s design assistants who I interviewed at a studio in London, England, for Elle magazine. When it came to tips for tricky dressing with prints and bold colours, she said, “I just throw them on and hope it works.” It’s that confident fearlessness that’s the key to wearing an outfit that may have people thinking you got dressed after indulging at that all-inclusive bar.

But you know what? Screw it! What’s the point in fashion if you can’t have fun with it? Don’t let the possibility of a few mistakes deter you from trying out something new.

What I Wore: vintage Wrangler jean jacket from Vintage Mix 1 on Ossington; vintage striped top from Shoppalu; vintage tropical print dress from St. Vincent de Paul in Forest, Ont.; shoes by Cacharel; sunglasses from St. Marks street in N.Y.C.; turquoise and gold cocktail ring by Yves Saint Laurent.